Real Estate Investment Properties for Sale in Longwood, FL

Looking for investment property in Longwood, FL with high ROI ?

Explore a variety of short-term homes & houses in Longwood, FL. Invest wisely with VRBO & Longwood, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Longwood, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3996 RADLEY COURT #3996 Longwood, FL One or more photo(s) has been virtually staged. MOTIVATED SELLER with an UNBELIEVABLE pric...	2 beds \| 2 baths \| 1,427 sq.ft.	$225,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 5.5% Airbnb Rental Income: $1600 Traditional Rental Income: $2287 Airbnb ROI: 0.14% Traditional ROI: 5.5%
417 SUMMIT RIDGE PLACE #213 Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully updated condo located ...	2 beds \| 2 baths \| 1,274 sq.ft.	$225,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.79% Airbnb Rental Income: $1600 Traditional Rental Income: $1871 Airbnb ROI: 0.38% Traditional ROI: 3.79%
276 W BAY AVENUE Longwood, FL Step into the timeless elegance of this beautifully crafted Victorian Home, newer construc...	3 beds \| 3 baths \| 1,814 sq.ft.	$419,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 3.8% Airbnb Rental Income: $2759 Traditional Rental Income: $2503 Airbnb ROI: 2.8% Traditional ROI: 3.8%
421 MEADOWRIDGE COVE Longwood, FL Welcome to this beautiful 4 bedroom 2 Â½ bath 2 STORY home in the exclusive gated communit...	4 beds \| 3 baths \| 3,048 sq.ft.	$650,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.88% Airbnb Rental Income: $2332 Traditional Rental Income: $2828 Airbnb ROI: 0.11% Traditional ROI: 1.88%
102 N SILVER CLUSTER COURT Longwood, FL Under contract-accepting backup offers. Welcome to 102 Silver Cluster Ct N in Longwood, a ...	3 beds \| 2 baths \| 1,166 sq.ft.	$383,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.2% Airbnb Rental Income: $2759 Traditional Rental Income: $1980 Airbnb ROI: 3.56% Traditional ROI: 3.2%
1870 CROWLEY CIRCLE E Longwood, FL Under contract-accepting backup offers. Short Sale. Approved Short Sale. Welcome to your p...	4 beds \| 4 baths \| 3,258 sq.ft.	$625,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 5.32% Airbnb Rental Income: $2332 Traditional Rental Income: $4618 Airbnb ROI: 0.41% Traditional ROI: 5.32%
884 CUTLER ROAD Longwood, FL One or more photo(s) has been virtually staged. - Price Improvement - Welcome to this beau...	5 beds \| 3 baths \| 2,601 sq.ft.	$599,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 1.98% Airbnb Rental Income: $5048 Traditional Rental Income: $2235 Airbnb ROI: 5.17% Traditional ROI: 1.98%
106 SPRINGWOOD CIRCLE #B Longwood, FL Under contract-accepting backup offers. Virtually Staged. This darling condo is located in...	2 beds \| 1 baths \| 1,020 sq.ft.	$148,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 8.45% Airbnb Rental Income: $1600 Traditional Rental Income: $1517 Airbnb ROI: 5.82% Traditional ROI: 8.45%
106 HIDDEN OAK DRIVE Longwood, FL Tucked beneath a canopy of towering oaks on a quiet, tucked-away street, this 3-bedroom, 2...	3 beds \| 2 baths \| 2,127 sq.ft.	$460,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 3.49% Airbnb Rental Income: $2759 Traditional Rental Income: $2525 Airbnb ROI: 2.53% Traditional ROI: 3.49%
478 SABAL TRAIL CIRCLE Longwood, FL NEW PRICE: As Of 6/15 : Welcome to the desirable Sabal Point community! Located at 478 S...	4 beds \| 3 baths \| 2,529 sq.ft.	$599,500	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.83% Airbnb Rental Income: $2332 Traditional Rental Income: $3502 Airbnb ROI: 0.71% Traditional ROI: 3.83%
300 NEW WATERFORD PLACE #202 Longwood, FL Perfect for First-Time Buyers or Those Ready to Downsize! Donât miss this rare opport...	2 beds \| 2 baths \| 1,176 sq.ft.	$269,900	Airbnb cash on cash: 2.25% Traditional cash on cash: 4.65% Airbnb Rental Income: $1600 Traditional Rental Income: $1754 Airbnb ROI: 2.25% Traditional ROI: 4.65%
2214 Earleaf Court Longwood, FL This stunning 4-bedroom, 3-bathroom home is nestled in a highly sought-after neighborhood,...	4 beds \| 3 baths \| 3,955 sq.ft.	$1,450,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.64% Airbnb Rental Income: $2332 Traditional Rental Income: $3572 Airbnb ROI: -0.71% Traditional ROI: 0.64%
860 Charlotte St. Longwood, FL 4-Bed / 3.5-Bath Home Built in 2006. -needs updating, new ac.	4 beds \| 4 baths \| N/A	$449,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 5.25% Airbnb Rental Income: $2332 Traditional Rental Income: $3324 Airbnb ROI: 1.52% Traditional ROI: 5.25%
1025 BUCKSAW PLACE Longwood, FL Short Sale. Short Sale â Opportunity awaits! This home has been winterized and is ready ...	3 beds \| 3 baths \| 2,289 sq.ft.	$419,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 6.1% Airbnb Rental Income: $2759 Traditional Rental Income: $3557 Airbnb ROI: 2.42% Traditional ROI: 6.1%
2040 E TRIANGLE DRIVE Longwood, FL Beautiful opportunity in the highly desirable Longwood area, perfectly located just minute...	3 beds \| 2 baths \| 1,283 sq.ft.	$340,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 3.59% Airbnb Rental Income: $2759 Traditional Rental Income: $1912 Airbnb ROI: 4.21% Traditional ROI: 3.59%
450 E WARREN AVENUE Longwood, FL Under contract-accepting backup offers. Situated on an oversized double lot in the heart o...	2 beds \| 1 baths \| 888 sq.ft.	$265,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 3.51% Airbnb Rental Income: $1600 Traditional Rental Income: $1587 Airbnb ROI: 1.74% Traditional ROI: 3.51%
1889 RANCHLAND TRAIL Longwood, FL Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home, perfectly situated ...	4 beds \| 3 baths \| 2,333 sq.ft.	$998,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 2.18% Airbnb Rental Income: $2332 Traditional Rental Income: $3601 Airbnb ROI: 0.19% Traditional ROI: 2.18%
207 LONESOME PINE DRIVE Longwood, FL Under contract-accepting backup offers. FANTASTIC OPPORTUNITY IN SWEETWATER OAKS! Nestled ...	4 beds \| 2 baths \| 1,908 sq.ft.	$559,900	Airbnb cash on cash: 1.07% Traditional cash on cash: 2.08% Airbnb Rental Income: $2332 Traditional Rental Income: $2281 Airbnb ROI: 1.07% Traditional ROI: 2.08%
965 BUCKSAW PLACE Longwood, FL Under contract-accepting backup offers. Welcome to this spacious 4-bedroom, 3-bath home in...	4 beds \| 3 baths \| 2,361 sq.ft.	$530,000	Airbnb cash on cash: 1% Traditional cash on cash: 3.36% Airbnb Rental Income: $2332 Traditional Rental Income: $2919 Airbnb ROI: 1% Traditional ROI: 3.36%
210 WEEPING ELM LANE Longwood, FL Rare Opportunity in Shadowood Village at The Springs! Welcome to this spacious 3-bedroom, ...	3 beds \| 2 baths \| 2,076 sq.ft.	$470,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 2.41% Airbnb Rental Income: $2759 Traditional Rental Income: $2022 Airbnb ROI: 2.61% Traditional ROI: 2.41%
101 CHERRY HILL CIRCLE Longwood, FL This 4 bedrooms/3 bathrooms home is ideal for families and those who enjoy entertaining. R...	4 beds \| 3 baths \| 2,359 sq.ft.	$699,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.49% Airbnb Rental Income: $2332 Traditional Rental Income: $2973 Airbnb ROI: 0.62% Traditional ROI: 2.49%
470 FREEMAN STREET Longwood, FL Under contract-accepting backup offers. Set on an oversized lot with Water VIEWS in the de...	4 beds \| 2 baths \| 2,261 sq.ft.	$475,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 4.75% Airbnb Rental Income: $2332 Traditional Rental Income: $3094 Airbnb ROI: 1.73% Traditional ROI: 4.75%
572 LAKE WILDMERE COVE Longwood, FL Here is your opportunity to own a true Turn Key Investment property.This almost new townho...	4 beds \| 5 baths \| 2,294 sq.ft.	$455,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 3.79% Airbnb Rental Income: $2332 Traditional Rental Income: $3121 Airbnb ROI: 0.58% Traditional ROI: 3.79%
284 ISLAND SOUND COURT Longwood, FL Step into refined elegance and effortless sophistication in this nearly new Dockside maste...	4 beds \| 3 baths \| 2,692 sq.ft.	$799,999	Airbnb cash on cash: 0.15% Traditional cash on cash: 1.67% Airbnb Rental Income: $2332 Traditional Rental Income: $2884 Airbnb ROI: 0.15% Traditional ROI: 1.67%
486 N PIN OAK PLACE #112 Longwood, FL Virtually Staged. Seller may consider buyer concessions if made in an offerWelcome to ...	2 beds \| 1 baths \| 959 sq.ft.	$187,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 7.19% Airbnb Rental Income: $1600 Traditional Rental Income: $1767 Airbnb ROI: 3.7% Traditional ROI: 7.19%
450 LONGMEADOW LANE Longwood, FL Excellent opportunity in Sabal Point. POOL house with two NEW HVACs. 4 bedrooms, 3.5 bathr...	4 beds \| 4 baths \| 2,623 sq.ft.	$509,900	Airbnb cash on cash: 1.64% Traditional cash on cash: 6.09% Airbnb Rental Income: $2332 Traditional Rental Income: $3873 Airbnb ROI: 1.64% Traditional ROI: 6.09%
556 LAKE WILDMERE COVE Longwood, FL MOTIVATED SELLER â MAJOR PRICE REDUCTION! Priced AGGRESSIVELY BELOW MARKET VALUE for an...	3 beds \| 3 baths \| 2,294 sq.ft.	$419,700	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.09% Airbnb Rental Income: $2759 Traditional Rental Income: $3120 Airbnb ROI: 2.52% Traditional ROI: 5.09%
1310 RIDGE ROAD Longwood, FL Welcome to your own private oasis in the highly desirable Longwood area! This beautifully ...	3 beds \| 2 baths \| 1,520 sq.ft.	$475,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 4.33% Airbnb Rental Income: $2759 Traditional Rental Income: $2881 Airbnb ROI: 2.6% Traditional ROI: 4.33%
123 TOMOKA TRAIL #123 Longwood, FL True Florida Paradise ! Possible owner financing is just an added bonus True gated and gua...	2 beds \| 2 baths \| 1,243 sq.ft.	$229,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 8.05% Airbnb Rental Income: $1600 Traditional Rental Income: $2269 Airbnb ROI: 2.88% Traditional ROI: 8.05%
420 SUMMIT RIDGE PLACE #200 Longwood, FL **This property qualifies for a closing cost credit up to $3,700 through the Sellerâs pr...	3 beds \| 2 baths \| 1,586 sq.ft.	$219,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 6.21% Airbnb Rental Income: $2759 Traditional Rental Income: $2499 Airbnb ROI: 4.33% Traditional ROI: 6.21%
605 WATER OAK LANE Longwood, FL Florida Dream Home on Over Half an Acre in One of Longwoodâs Most Desirable Neighborhood...	3 beds \| 2 baths \| 1,831 sq.ft.	$499,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.17% Airbnb Rental Income: $2759 Traditional Rental Income: $2523 Airbnb ROI: 2.28% Traditional ROI: 3.17%
895 Pasadena Ave. Longwood, FL Unique Large Duplex, 1 unit faces Highland St and 1 unit faces Pasadena Ave,Large Corner L...	6 beds \| 4 baths \| N/A	$490,000	Airbnb cash on cash: 6.78% Traditional cash on cash: 6.87% Airbnb Rental Income: $5048 Traditional Rental Income: $4056 Airbnb ROI: 6.78% Traditional ROI: 6.87%
495 HOWARD AVENUE Longwood, FL Under contract-accepting backup offers. Back on market! Welcome home! This stunning 4-bedr...	4 beds \| 2 baths \| 1,855 sq.ft.	$409,999	Airbnb cash on cash: 2.73% Traditional cash on cash: 4.74% Airbnb Rental Income: $2332 Traditional Rental Income: $2527 Airbnb ROI: 2.73% Traditional ROI: 4.74%
2208 COVE COURT Longwood, FL Under contract-accepting backup offers. This stunning Lake Brantley estate combines timele...	5 beds \| 5 baths \| 3,404 sq.ft.	$1,500,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 2.79% Airbnb Rental Income: $5048 Traditional Rental Income: $6386 Airbnb ROI: 1.09% Traditional ROI: 2.79%
901 CUTLER ROAD Longwood, FL Pull over HONEY! This home is move it ready. Roof. 2023. AC 1 2020, AC 2 2022. Look at the...	3 beds \| 2 baths \| 2,226 sq.ft.	$525,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.23% Airbnb Rental Income: $2759 Traditional Rental Income: $2767 Airbnb ROI: 1.89% Traditional ROI: 3.23%
421 SUMMIT RIDGE PLACE #209 Longwood, FL Welcome to the gated community of Residences at Sabal Point, where comfort, convenience, a...	1 beds \| 1 baths \| 948 sq.ft.	$144,900	Airbnb cash on cash: 1.9% Traditional cash on cash: 7.62% Airbnb Rental Income: $1368 Traditional Rental Income: $1745 Airbnb ROI: 1.9% Traditional ROI: 7.62%
710 East Court Longwood, FL Welcome to this well-maintained property located in the heart of Longwood! This home offer...	4 beds \| 2 baths \| 1,533 sq.ft.	$340,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 5.73% Airbnb Rental Income: $2332 Traditional Rental Income: $2534 Airbnb ROI: 3.29% Traditional ROI: 5.73%
672 MOSSY BRANCH COURT Longwood, FL Completely remodeled and move-in ready, this impressive residence at 672 Mossy Branch Ct, ...	4 beds \| 3 baths \| 3,924 sq.ft.	$775,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.24% Airbnb Rental Income: $2332 Traditional Rental Income: $3606 Airbnb ROI: 0.67% Traditional ROI: 3.24%
1126 BROWNSHIRE COURT Longwood, FL This majestic estate is a true masterpiece of elegance and timeless architecture, graceful...	5 beds \| 7 baths \| 8,100 sq.ft.	$2,598,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.77% Airbnb Rental Income: $5048 Traditional Rental Income: $10650 Airbnb ROI: 0.02% Traditional ROI: 2.77%
7102 OLYMPIA COURT #7102 Longwood, FL Welcome home! NEW PRICE! AND DONâT MISS THIS FACT: FURNITURE INCLUDED! This beautifully...	2 beds \| 3 baths \| 1,365 sq.ft.	$255,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 6.01% Airbnb Rental Income: $1600 Traditional Rental Income: $1975 Airbnb ROI: 2.56% Traditional ROI: 6.01%

Real Estate investment in Longwood, FL

There are 122 properties for sale in the city of Longwood . The median list price in Longwood is $369,779 and the average price per square foot is $168. In July 2026, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,455.

Longwood, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 122 investment properties available for sale in Longwood.

In 2026, the best neighborhood to buy investment property is Longwood.

The ROI for Long-Term is higher than the Short-Term in Longwood with average rental income of $2,455.

Your search for investment property begins and ends here

Investment Property for Sale in Longwood, FL

3996 RADLEY COURT #3996

Longwood, FL

2 beds | 2 baths | 1,427 sq.ft.

$225,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1600

Traditional Rental Income: $2287

Airbnb ROI: 0.14%

Traditional ROI: 5.5%

417 SUMMIT RIDGE PLACE #213

Longwood, FL

2 beds | 2 baths | 1,274 sq.ft.

$225,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $1600

Traditional Rental Income: $1871

Airbnb ROI: 0.38%

Traditional ROI: 3.79%

276 W BAY AVENUE

Longwood, FL

3 beds | 3 baths | 1,814 sq.ft.

$419,000

Airbnb cash on cash: 2.8%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $2759

Traditional Rental Income: $2503

Airbnb ROI: 2.8%

Traditional ROI: 3.8%

421 MEADOWRIDGE COVE

Longwood, FL

4 beds | 3 baths | 3,048 sq.ft.

$650,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $2332

Traditional Rental Income: $2828

Airbnb ROI: 0.11%

Traditional ROI: 1.88%

102 N SILVER CLUSTER COURT

Longwood, FL

3 beds | 2 baths | 1,166 sq.ft.

$383,000

Airbnb cash on cash: 3.56%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $2759

Traditional Rental Income: $1980

Airbnb ROI: 3.56%

Traditional ROI: 3.2%

1870 CROWLEY CIRCLE E

Longwood, FL

4 beds | 4 baths | 3,258 sq.ft.

$625,000

Airbnb cash on cash: 0.41%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $2332

Traditional Rental Income: $4618

Airbnb ROI: 0.41%

Traditional ROI: 5.32%

884 CUTLER ROAD

Longwood, FL

5 beds | 3 baths | 2,601 sq.ft.

$599,000

Airbnb cash on cash: 5.17%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $5048

Traditional Rental Income: $2235

Airbnb ROI: 5.17%

Traditional ROI: 1.98%

106 SPRINGWOOD CIRCLE #B

Longwood, FL

2 beds | 1 baths | 1,020 sq.ft.

$148,000

Airbnb cash on cash: 5.82%

Traditional cash on cash: 8.45%

Airbnb Rental Income: $1600

Traditional Rental Income: $1517

Airbnb ROI: 5.82%